D-Azetidine-2-carboxylic acid

Base Information

• Chemical Name: D-Azetidine-2-carboxylic acid
• CAS No.: 7729-30-8
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• Hs Code.: 29339900
• Mol file: 7729-30-8.mol

Synonyms:2-Azetidinecarboxylicacid, (R)-;2-Azetidinecarboxylic acid, D- (8CI);(+)-Azetidinecarboxylic acid;(R)-Azetidine-2-carboxylic acid;D-2-Azetidinecarboxylic acid;(2R)-(+)-Azetidine-2-carboxylic acid;

Chemical Property of D-Azetidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.0116mmHg at 25°C
• Melting Point: 209-211 °C
• Refractive Index: 1.499
• Boiling Point: 242 °C at 760 mmHg
• PKA: 2.35±0.20(Predicted)
• Flash Point: 100.1 °C
• PSA: 49.33000
• Density: 1.275 g/cm³
• LogP: -0.23830
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

D-Azetidine-2-Carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: D-Azetidine-2-Carboxylic Acid is a four-membered ring analog of L-Proline. A useful intermediate in the synthesis of polypeptides

Technology Process of D-Azetidine-2-carboxylic acid

There total 6 articles about D-Azetidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyl [1(1S,2R)]-1-(1-phenyl-ethyl)-azetidine-2-carboxylate (249734-37-0) → (R)-azetidine-2-carboxylic acid (7729-30-8,20063-89-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 96h;

DOI:10.1021/jo0515881

Reference yield: 95.0%

methyl (2R,αR)-N-α-methylbenzylazetidine-2-carboxylate (186096-46-8) → (R)-azetidine-2-carboxylic acid (7729-30-8,20063-89-2)

Guidance literature:

methyl (2R,αR)-N-α-methylbenzylazetidine-2-carboxylate; With hydrogenchloride;

With palladium dihydroxide; hydrogen;

DOI:10.1016/j.tetlet.2006.11.033

Reference yield: 88.0%

→ (R)-azetidine-2-carboxylic acid (7729-30-8,20063-89-2)

Guidance literature:

upstream raw materials:

L-2,4-diaminobutyrate

(2R,2S)-1-benzyloxycarbonylazetidine-2-carboxylic acid

benzyl [1(1S,2R)]-1-(1-phenyl-ethyl)-azetidine-2-carboxylate

(R)-1-((S)-1-Phenyl-ethyl)-azetidine-2-carboxylic acid; hydrochloride

Downstream raw materials:

(2R,2S)-1-benzyloxycarbonylazetidine-2-carboxylic acid

(R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)azetidine-2-carboxylic acid

C₆H₆F₃NO₃

(R)-1-{5-[4-(3-chlorophenyl)-2-methylbenzothiazol-6-ylmethyl]pyridin-2-yl}azetidine-2-carboxylic acid

Refernces

• 1、 Couty, Francois,Evano, Gwilherm,Vargas-Sanchez, Monica,Bouzas, Gloria. "Practical asymmetric preparation of azetidine-2-carboxylic acid". . p. 9028 - 9031. Retrieved 2007/10/03.
• 2、 Holladay, Mark W.,Wasicak, James T.,Lin, Nan-Horng,He, Yun,Ryther, Keith,Bannon, Anthony W.,Buckley, Michael J.,Kim, David J. B.,Decker, Michael W.,Anderson, David J.,Campbell, Jeffrey E.,Kuntzweiler, Theresa A.,Donnelly-Roberts, Diana L.,Piattoni-Kaplan, Marietta,Briggs, Clark A.,Williams, Michael,Arneric, Stephen P.. "Identification and initial structure-activity relationships of (R)-5- (2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors". . p. 407 - 412. Retrieved 2007/10/03.